[go: up one dir, main page]

EP0645374B1 - Compose 5-amino-2-phenoxylsulfonanilide - Google Patents

Compose 5-amino-2-phenoxylsulfonanilide Download PDF

Info

Publication number
EP0645374B1
EP0645374B1 EP93909405A EP93909405A EP0645374B1 EP 0645374 B1 EP0645374 B1 EP 0645374B1 EP 93909405 A EP93909405 A EP 93909405A EP 93909405 A EP93909405 A EP 93909405A EP 0645374 B1 EP0645374 B1 EP 0645374B1
Authority
EP
European Patent Office
Prior art keywords
compound
sodium
amino
reaction
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP93909405A
Other languages
German (de)
English (en)
Other versions
EP0645374A1 (fr
EP0645374A4 (fr
Inventor
Kensei Taisho Pharmaceutical Co. Ltd. Yoshikawa
Shuji Taisho Pharmaceutical Co. Ltd. Saito
Yohichi Taisho Pharmaceutical Co. Ltd. Shimazaki
Mariko Taisho Pharmaceutical Co. Ltd. Kashiwa
Katsuo Taisho Pharmaceutical Co. Ltd. Hatayama
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Taisho Pharmaceutical Co Ltd
Original Assignee
Taisho Pharmaceutical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Taisho Pharmaceutical Co Ltd filed Critical Taisho Pharmaceutical Co Ltd
Publication of EP0645374A4 publication Critical patent/EP0645374A4/fr
Publication of EP0645374A1 publication Critical patent/EP0645374A1/fr
Application granted granted Critical
Publication of EP0645374B1 publication Critical patent/EP0645374B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

Definitions

  • the present invention relates to a 5-amino-2-phenoxysulfonanilide compound having anti-inflammatory, antipyretic, analgesic and antirheumatic actions.
  • An object of the present invention is to provide drugs having excellent anti-inflammatory, antipyretic, analgesic and antirheumatic actions.
  • the present invention relates to a 5-amino-2-phenoxysulfonanilide compound represented by Formula (I): and to pharmaceutically acceptable salts thereof.
  • the salt refers to salts with alkali metals (e.g. sodium and potassium), alkaline earth metals (e.g. calcium and magnesium), ammonia and organic bases (e.g. ethanolamine, lysine and arginine).
  • alkali metals e.g. sodium and potassium
  • alkaline earth metals e.g. calcium and magnesium
  • ammonia and organic bases e.g. ethanolamine, lysine and arginine.
  • the compound of Formula (I) of the present invention can be prepared, for example, by the following preparation steps (a) to (f).
  • the hydrolysis in this reaction may be a conventional hydrolysis of an amide under the basic or acidic condition, for example, a hydrolysis using lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, sodium ethoxide or potassium t-butoxide for the basic condition, or a hydrolysis using hydrochloric acid, hydrobromic acid or sulfuric acid for the acidic condition.
  • Examples of the solvent to be used in the reaction are water, methanol, ethanol, propanol, t-butanol, tetrahydrofuran, dioxane, benzene, toluene, xylene, chlorobenzene, N,N-dimethylformamide, dimethyl sulfoxide, formic acid and acetic acid, but it is preferably that the solvent is appropriately chosen depending on the condition of the hydrolysis.
  • the compound of the present invention can be administered orally or parenterally in the conventional dosage forms such as, for example, tablets, dusts, granules, powders, capsules, solutions, emulsions, suspensions and injections, all of which can be prepared by conventional practices.
  • the dose used for humans as an anti-inflammatory, antipyretic, analgesic or antirheumatic agent is different depending on the age and body weight of the patient, symptoms of the disease, route of administration and frequency of administration, but it is usually from 5 to 600 mg per day.
  • the compound which is an active ingredient in the present invention has potent anti-inflammatory, antipyretic, analgesic and antirheumatic actions with fewer side effects such as gastrointestinal disorders, and therefore it is useful as anti-inflammatory, antipyretic, analgesic or antirheumatic agents.
  • test drugs the compound (a) of the present invention and the control drug (b)
  • test drugs each suspended in 5% aqueous gum arabic solution in an amount of 1 ml per 100 g of body weight.
  • 0.1 ml of 1% carrageenin was administered subcutaneously into the left hind foot pad.
  • the volume of the foot was determined, and the edema inhibition rate (%) was calculated for the anti-inflammatory effect.
  • Dose of the test drug was 0.3 mg/kg.
  • mice Seven Lewis strain rats (for each group) were administered subcutaneously 0.7% Mycobacterium tuberculosis suspended in liquid paraffin into the left hind foot pad to induce adjuvant arthritis. 15 ⁇ 18 Days after administration of adjuvant, rats with fully developed arthritis were administered orally with test drugs [the compound (a) of the present invention and the control compound (b)], each suspended in 5% aqueous gum arabic solution in an amount of 1 ml per 100 g of body weight once a day for 4 days.
  • test drugs the compound (a) of the present invention and the control compound (b)
  • the volume of the foot was determined, and the edema inhibition rate (%) was calculated for the therapeutical effect.
  • Dose of the test drug was 0.2 mg/kg.
  • test drugs the compound (a) of the present invention and the control compound (b)
  • test drugs each suspended in 5% aqueous gum arabic solution in an amount of 1 ml per 100 g of body weight.
  • the occurrence of squeaking response was monitored with time over 5 hours after the administration, and the inhibition rate (%) was calculated to examine the analgesic effect.
  • Dose of the test drug was 1.0 mg/kg.
  • the compound (a) of the present invention the compound of Example 1.
  • Control compound (b) N-(4-nitro-2-phenoxyphenyl)methanesulfonamide
  • Healthy human peripheral blood heparinized was layered over Lymphoprep (Daiichi Pharmaceutical Co.) under aseptic conditions to remove red blood cell, and the cell counts were adjusted to 2 ⁇ 10 6 cells/ml by froating the cells in RPMI-1640 medium containing 10% fatal bovine serum, penicillin 100U/ml, streptomycin 100U/ml, HEPES buffer 10mM and L-glutamin 2mM.
  • the concentrations of the test drug were 0, 3, 10 and 30 ⁇ g/ml.
  • IC 50 value of the 1L-1 formation inhibiting action of the compound (a) of the present invention was 13.3 ⁇ g/ml, but the control compound (b) did not show 50% or more inhibition in the above concentration, and therefore the IC 50 value could not be calculated.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Claims (2)

  1. Composé représenté par la formule:
    Figure imgb0015
     ou un sel de celui-ci.
EP93909405A 1992-06-12 1993-04-21 Compose 5-amino-2-phenoxylsulfonanilide Expired - Lifetime EP0645374B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP15255492 1992-06-12
JP152554/92 1992-06-12
PCT/JP1993/000518 WO1993025520A1 (fr) 1992-06-12 1993-04-21 Compose 5-amino-2-phenoxylsulfonanilide

Publications (3)

Publication Number Publication Date
EP0645374A4 EP0645374A4 (fr) 1995-02-14
EP0645374A1 EP0645374A1 (fr) 1995-03-29
EP0645374B1 true EP0645374B1 (fr) 1996-11-20

Family

ID=15543009

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93909405A Expired - Lifetime EP0645374B1 (fr) 1992-06-12 1993-04-21 Compose 5-amino-2-phenoxylsulfonanilide

Country Status (11)

Country Link
US (1) US5449826A (fr)
EP (1) EP0645374B1 (fr)
KR (1) KR0150826B1 (fr)
AT (1) ATE145395T1 (fr)
AU (1) AU661906B2 (fr)
CA (1) CA2137780C (fr)
DE (1) DE69306113T2 (fr)
DK (1) DK0645374T3 (fr)
ES (1) ES2097505T3 (fr)
GR (1) GR3021821T3 (fr)
WO (1) WO1993025520A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994019318A1 (fr) * 1993-02-19 1994-09-01 Taisho Pharmaceutical Co., Ltd. Compose de 5-aminoacetylaminosulfonanilide
DE19533644A1 (de) * 1995-09-12 1997-03-13 Nycomed Arzneimittel Gmbh Neue Benzolsulfonamide
DE19533643A1 (de) * 1995-09-12 1997-03-13 Nycomed Arzneimittel Gmbh Neue cyclische Derivate von Benzolsulfonamiden

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3531552A (en) * 1967-05-04 1970-09-29 Eaton Yale & Towne Method of making composite load supporting structure
US3840597A (en) * 1971-02-24 1974-10-08 Riker Laboratories Inc Substituted 2-phenoxy alkane-sulfonanilides
US3856859A (en) * 1973-06-08 1974-12-24 Riker Laboratories Inc Selective nitration process
PT86407B (pt) * 1986-12-31 1990-11-20 Fujisawa Pharmaceutical Co Processo para a preparacao de novos derivados de alcano-sulfonanilida, e de composicoes farmaceuticas compreendendo os mesmos
GB8631083D0 (en) * 1986-12-31 1987-02-04 Fujisawa Pharmaceutical Co 2'-phenoxyalkanesulfonanilide derivatives
US4885367A (en) * 1987-11-19 1989-12-05 Taisho Pharmaceutical Co., Ltd. Sulfonanilide compounds
JPH0611747B2 (ja) * 1987-11-19 1994-02-16 大正製薬株式会社 スルホンアニリド化合物
JPH0222260A (ja) * 1988-07-11 1990-01-25 Taisho Pharmaceut Co Ltd 置換スルホンアニリド
JPH02300122A (ja) * 1989-05-12 1990-12-12 Taisho Pharmaceut Co Ltd 消炎・鎮痛・解熱剤
EP0641774B1 (fr) * 1991-08-08 1996-05-08 Taisho Pharmaceutical Co. Ltd Compose 5-aminosulfonanilide
WO1994019318A1 (fr) * 1993-02-19 1994-09-01 Taisho Pharmaceutical Co., Ltd. Compose de 5-aminoacetylaminosulfonanilide

Also Published As

Publication number Publication date
EP0645374A1 (fr) 1995-03-29
KR0150826B1 (ko) 1998-10-15
EP0645374A4 (fr) 1995-02-14
WO1993025520A1 (fr) 1993-12-23
DE69306113T2 (de) 1997-03-13
DE69306113D1 (de) 1997-01-02
CA2137780C (fr) 1998-06-09
AU4022493A (en) 1994-01-04
CA2137780A1 (fr) 1993-12-23
US5449826A (en) 1995-09-12
ES2097505T3 (es) 1997-04-01
AU661906B2 (en) 1995-08-10
ATE145395T1 (de) 1996-12-15
GR3021821T3 (en) 1997-02-28
DK0645374T3 (da) 1996-12-23
KR950701617A (ko) 1995-04-28

Similar Documents

Publication Publication Date Title
AU660854B2 (en) New arylalkyl (thio)amides, process for preparing them and pharmaceutical compositions containing them
US20080293939A1 (en) Quinazolinone derivatives useful as anti-hyperalgesic agents
US4689182A (en) Benzoic acid and benzoic acid ester derivatives having anti-inflammatory and analgesic activity
RU2727194C2 (ru) Гетероциклические соединения для лечения заболевания
JP2004504323A (ja) インドロキナゾリノン類
EP0645374B1 (fr) Compose 5-amino-2-phenoxylsulfonanilide
EP0623023A1 (fr) Analogues retroverses d'agents anticancereux a oligopeptides de pyrrole-amidino, leur procede de preparation, et compositions pharmaceutiques contenant ces analogues
US3576866A (en) Benzoylhaloalkanesulfonanilides
EP0641774B1 (fr) Compose 5-aminosulfonanilide
US4755518A (en) Imidazolyl or tetrazolyl substituted benzoic acid derivatives and pharmaceutical compositions thereof
CS207785B2 (en) Method of making the derivatives of the n-phenylalanine or n-phenylglycine
JP2668009B2 (ja) ５−アミノ−２−フェノキシスルホンアニリド化合物
US5521311A (en) 5-aminoacetylaminosulfonanilide compounds
JP3721583B2 (ja) 抗炎症剤
US4980366A (en) Amide, sulfonamide, urea, carbamate, thiocarbamate, and thiourea derivatives of 4'hydroxybenzylamine having anti-inflammatory and analgesic activity
EP0262618A2 (fr) N-[(oméga)-cyanoalkyl]aminophénols et leur préparation
US6919328B1 (en) Tricyclic compounds with NOS activity
US4719234A (en) Benzoic acid and benzoic acid ester derivatives to treat inflammation
US4719232A (en) Benzoic acid and benzoic acid ester derivatives to treat headaches
JPH0672988A (ja) ５−アミノ−２−ハロフェノキシスルホンアニリド化合物
JPS649989B2 (fr)
US4719233A (en) Benzoic acid and benzoic acid ester derivatives to treat pain
JPH06298722A (ja) ５−アミノアセチルアミノスルホンアニリド化合物
US5002703A (en) Benzoic acid and benzoic acid ester derivatives having antiinflammatory and analgesic activity
JPS6141333B2 (fr)

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

A4 Supplementary search report drawn up and despatched
AK Designated contracting states

Kind code of ref document: A4

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL PT SE

17P Request for examination filed

Effective date: 19941208

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL PT SE

RIN1 Information on inventor provided before grant (corrected)

Inventor name: HATAYAMA, KATSUO TAISHO PHARMACEUTICAL CO., LTD.

Inventor name: KASHIWA, MARIKO TAISHO PHARMACEUTICAL CO., LTD.

Inventor name: SHIMAZAKI, YOHICHI TAISHO PHARMACEUTICAL CO., LTD

Inventor name: SAITO, SHUJI TAISHO PHARMACEUTICAL CO., LTD.

Inventor name: YOSHIKAWA, KENSEI TAISHO PHARMACEUTICAL CO., LTD.

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

17Q First examination report despatched

Effective date: 19951228

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL PT SE

REF Corresponds to:

Ref document number: 145395

Country of ref document: AT

Date of ref document: 19961215

Kind code of ref document: T

ITF It: translation for a ep patent filed
REG Reference to a national code

Ref country code: CH

Ref legal event code: NV

Representative=s name: NOVAPAT INTERNATIONAL S.A.

ET Fr: translation filed
REG Reference to a national code

Ref country code: DK

Ref legal event code: T3

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

Free format text: 70715

REF Corresponds to:

Ref document number: 69306113

Country of ref document: DE

Date of ref document: 19970102

REG Reference to a national code

Ref country code: GR

Ref legal event code: FG4A

Free format text: 3021821

REG Reference to a national code

Ref country code: PT

Ref legal event code: SC4A

Free format text: AVAILABILITY OF NATIONAL TRANSLATION

Effective date: 19961120

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2097505

Country of ref document: ES

Kind code of ref document: T3

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: PT

Payment date: 20000405

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 20000406

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20000411

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DK

Payment date: 20000412

Year of fee payment: 8

Ref country code: AT

Payment date: 20000412

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GR

Payment date: 20000417

Year of fee payment: 8

Ref country code: DE

Payment date: 20000417

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: LU

Payment date: 20000419

Year of fee payment: 8

Ref country code: GB

Payment date: 20000419

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IE

Payment date: 20000426

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 20000427

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20000428

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: MC

Payment date: 20000502

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 20000622

Year of fee payment: 8

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010421

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010421

Ref country code: DK

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010421

Ref country code: AT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010421

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010422

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010423

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MC

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010430

Ref country code: GR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010430

Ref country code: FR

Free format text: THE PATENT HAS BEEN ANNULLED BY A DECISION OF A NATIONAL AUTHORITY

Effective date: 20010430

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010430

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20010430

Year of fee payment: 9

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010520

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010520

BERE Be: lapsed

Owner name: TAISHO PHARMACEUTICAL CO. LTD

Effective date: 20010430

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: PT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20011031

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20011101

EUG Se: european patent has lapsed

Ref document number: 93909405.8

REG Reference to a national code

Ref country code: DK

Ref legal event code: EBP

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20010421

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 20011101

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20020201

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

REG Reference to a national code

Ref country code: IE

Ref legal event code: MM4A

REG Reference to a national code

Ref country code: PT

Ref legal event code: MM4A

Free format text: LAPSE DUE TO NON-PAYMENT OF FEES

Effective date: 20011031

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20020422

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20030514

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.

Effective date: 20050421